Room with a View: The Best Hotels in San Juan, Puerto Rico

The oldest city under U.S. jurisdiction has aged with unbeatable finesse and charm. The city was founded way back in 1521 by explorer Ponce de León, of Fountain of Youth notoriety. Roads were paved with adoquine cobbles brought over by Spanish ships that still glimmer vibrant blue under the heat of the San Juan sun. These distinctive tiles have been leading visitors astray for hundreds of years, distracted by the pastel color palette, secret gardens and impressive colonial architecture. 

Views of the Atlantic abound from almost any vantage point, including the rooftop patios and classic shuttered door balconies that many San Juan hotels boast. From ambling down the adoquines to stretching out oceanside, San Juan offers the best of culture, sea and sun without the bother of a passport.

Photos from trivago.

Photos from trivago.

Drawing on the eclectic history of San Juan, the CasaBlanca Hotel is brimming with charismatic touches. Located in the heart of Old San Juan, the vibe here is altogether antiquated romantic. Each room has been lovingly decorated with beds bedecked in white canopied curtains and the walls playing host to paintings from local artists. You’ll get picturesque views of all of San Juan’s best angles from the 24-hour rooftop terrace soaking tubs. We recommend a sunrise soak with that view before enjoying your complimentary breakfast. 

Photos from trivago.

The Villa Herencia Hotel is tucked away in the cool shadowed streets of San Juan’s oldest neighborhood. The boutique hotel’s eight rooms are all uniquely furnished with a mix of antiques and modern classics with the odd touch of zebra print and luminous jewel tones. The hotel’s historic architecture hardly plays second fiddle to the funky vibe of the decor; high ceiling, tiled floors and shuttered windows swing you back to the building’s 1885 foundation. Nearby you can get a delicious jug of sangria and a plate of tapas at Patio De Ana or slurp ice cream in the Plaza de la Catedral.

Photos from trivago.

Close enough to feel the spray of the Atlantic Ocean, the Hyatt House San Juan sits you comfortably in the Miramar neighborhood of San Juan. The proximity to the sea make for fantastic views from many of the suites, equipped also with kitchens, plush beds and free WiFi. A sumptuous breakfast comes complimentary and includes goodies like the chef-created omelettes from cage-free eggs, all natural bacon and sausages, steel cut oats and Greek yogurt. An impressive pool area beckons visitors to its ample loungers and greenery. This is a fantastic pre- and post-cruise San Juan hotel choice or for those looking to linger long-term in the sunny port city.

Photos from trivago.

In 1646, construction started on this former Carmelite convent. After 252 years, they pulled the plug on religion and converted the building into a hotel in 1962. Today, it proudly bears the name Hotel El Convento and an unbeatable location among the prettiest of Old San Juan’s cobblestoned streets. Better yet, guests receive access to the El Convento Beach Club at the sister property down on the beach. Two onsite restaurants see you sampling Spanish tapas one night and dining al fresco for breakfast, lunch or dinner under the shade of the Nispero tree. Rooms are decorated with ornate bespoke furnishing and cool marble bathrooms with bold walnut or mahogany exposed beams.

Photos from trivago.

Step inside the home of a true San Juan artist with a stay at The Gallery. Housed inside six townhouses sandwiches together by brick patios, fountains and ancient walls, Barack and Michelle Obama count themselves as fans of this unique property. Wind your way through 19 gardens, peek into active art studios and stop for a chat with Campeche, a Moluccan Cockatoo with a cheeky personality. A free continental breakfast is included in your stay, as are the beautiful city and ocean views from the rooftop deck. You’ll sleep like royalty on the Tempur-Pedic mattresses under the damask canopies of four-poster beds.

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With its eye-catching modern facade, the striking Dream Inn heads in a very different direction to other similar boutique hotels in San Juan. A modern zen vibe resonates among the crisp concrete walls softened by the mid-century modern furniture, a colorful Koi pond and waterfall and the tropical palette of the rooms. You’re a six-minute walk from frolicking in the waves of Ocean Park Beach or if sand isn’t your thing, you can always retreat to the Inn’s terrace and pool. A free breakfast is available for guests at the nearby Kasalta Bakery, and a parking lot accommodates those coming by vehicle also without extra charges.

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If “beach” is the first word on your lips as soon as you wake up, the laid back Numero Uno Guest House should be your choice accommodation in San Juan. Located along a stunning long stretch of soft sand and crystal clear waters of Ocean Park Beach, the views of the Atlantic and its dramatic sunsets are the biggest draw for the property. What could pack more romantic punch than proposing during a sunset beachfront dinner from onsite restaurant Pamela’s Caribbean Cuisine? The food at Pamela’s isn’t merely a touristic beach trap, but the kind of place that welcomes locals regularly. You’ll also wake up to a free continental breakfast and enjoy free WiFi.

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Unleash your inner earth-loving hippie spirit at The Dreamcatcher, a vegetarian bed and breakfast also accommodating vegans. The property entices with good vibes that let you sink straight into relaxation mode with yoga classes, free beach chairs and umbrellas and a very short jaunt to the beach. The property is bejeweled by an impressive collection of hammocks dotting all the most attractive corners of this Bohemian-inspired stay with potted plants, cacti and fruit trees all ushering nature inside. Breakfast is available at an additional cost but delights with several courses of vegan or vegetarian fare served in a dining room overlooking the garden.

Photos from trivago.

Located in the Condado district of San Juan, La Concha Renaissance is a modernist stay perfect for those looking for a bit of South Beach-style vacation glitz. Dazzling ocean views from many of the rooms do not disappoint (despite the view surcharge) while rain showerheads strip away any signs of salty water with Aveda bath products. The lobby moves from coffee and pastries to espresso coffee and salads to a full on party at night, complete with trendy guests turned out in high heels and lounging in the seating areas. During daylight hours, three separate pools including one adults-only infinity pool are the place to be seen. Several dining options including sushi, tapas and high-end seafood follow along with the contemporary vibe of La Concha.